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Hampshire 276 and 84 for 5 need a further 85 runs to beat Nottinghamshire 235 and 209 (Haynes 59, Clarke 57, Organ 3-38, Abbott 3-41)
Hampshire's opportunity to notch a first win of the season is in the balance after a fast-moving third day of their Vitality County Championship match at Trent Bridge left them with still much work to do.
Chasing a modest 169 to win, Hampshire ended the day still 85 runs away from their target at 84 for 5 and probably a man short unless Tom Prest can bat with the injured shoulder that has kept him off the field since tea on day one.
Nottinghamshire had been bowled out for 209 in their second innings by tea, with veteran quick Kyle Abbott and offspinner Felix Organ taking three wickets each after Joe Clarke and Jack Haynes had made half-centuries.
But Hampshire then slumped to 44 for 5 as Dillon Pennington and Dane Paterson led a determined effort with the ball by the home side before Fletcha Middleton and James Fuller saw out the final overs to calm their nerves.
Still eight runs behind at 33 for 1 overnight, Nottinghamshire stumbled into early trouble as the pattern of the first two innings repeated itself.
Against a ball that was only 15 overs old, they lost wickets in each of Abbott's opening three overs. Will Young edged to wicketkeeper Ben Brown from a ball that lifted and left him, Ben Slater was pushed back in his crease to be leg before and Tom Moores saw his off stump uprooted by one angled in from wide by the veteran South African seamer.
At 44 for 4 - effectively 3 for 4 - Nottinghamshire were in a difficult spot that could have turned worse still had Clarke not been dropped on 17 at 65 for 4. It was Michael Neser at first slip - substitute for the injured Prest - whose hands let him down, a second such error of the match by the Australian and a fifth for Hampshire overall.
Clarke punished the mistake by passing fifty for the fourth time this season as he and Haynes added 96 for the fifth wicket before the former was out for 57, gloving a catch to Brown after being tempted by a short delivery from Mohammad Abbas.
Haynes completed his half-century from 111 balls, but against the spin combination of Liam Dawson and Organ on a three-day old pitch Nottinghamshire's hopes of building a substantial lead unravelled.
Organ struck the first blow as Haynes was caught at short leg via an inside edge on to pad, picking up a second when Lyndon James, trying to help one round the corner, gave an easy catch to short fine leg.
Dawson then claimed two in consecutive overs as Olly Stone's paddle sweep looped up gently for James Vince to catch running across from slip before Dillon Pennington was trapped leg before. Organ wrapped things up by having Calvin Harrison stumped, leaving Hampshire needing 169 to win.
With Nick Gubbins missing the match on paternity leave and Prest unlikely to bat, it was never likely to be a straightforward task against the Nottinghamshire attack, even with 127 overs at their disposal.
Knowing the potency of the new ball so far in this contest, Hampshire made no attempt to hurry yet still found themselves two down for 15 inside the first 10 overs, thanks to two superlative catches.
Nottinghamshire captain Haseeb Hameed took the first, plucking the ball out of the air one-handed at mid-on as Ali Orr mistimed his shot horribly against Pennington, who picked up his second wicket soon afterwards.
This time Harrison produced the athleticism, using every inch of his 6ft 4ins plus a fully extended right arm to grab the ball a good eight feet off the ground. Organ, the man out, had aimed a rather wild slash at a ball wide of off stump but was nonplussed nonetheless that it had not cleared the cordon.
It was enough for Nottinghamshire to sense an opportunity and they took full advantage of Hampshire's frailty.
Skipper Vince, on whom much seemed to rest, fell for 6, leg before to a full delivery from Paterson that he was trying to work to leg, Dawson hit James straight into the hands of short cover and Brown lost his off stump to a swinging delivery from Paterson, leaving Hampshire 44 for 5 and facing a fight for survival.
